WO2000008495A3 - Antiproliferative naphthoquinones, derivatives, compositions, and uses thereof - Google Patents

Antiproliferative naphthoquinones, derivatives, compositions, and uses thereof Download PDF

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Publication number
WO2000008495A3
WO2000008495A3 PCT/US1999/017863 US9917863W WO0008495A3 WO 2000008495 A3 WO2000008495 A3 WO 2000008495A3 US 9917863 W US9917863 W US 9917863W WO 0008495 A3 WO0008495 A3 WO 0008495A3
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
different
same
heteroatom
heterocyclic
Prior art date
Application number
PCT/US1999/017863
Other languages
French (fr)
Other versions
WO2000008495A2 (en
Inventor
Brian I Carr
Craig S Wilcox
Jeffrey K Kerns
Original Assignee
Univ Pittsburgh
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Univ Pittsburgh filed Critical Univ Pittsburgh
Priority to AU53416/99A priority Critical patent/AU5341699A/en
Publication of WO2000008495A2 publication Critical patent/WO2000008495A2/en
Publication of WO2000008495A3 publication Critical patent/WO2000008495A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
    • C07C205/46—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group the carbon skeleton containing carbon atoms of quinone rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/30—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms
    • C07C233/33—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C46/00—Preparation of quinones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C46/00—Preparation of quinones
    • C07C46/02—Preparation of quinones by oxidation giving rise to quinoid structures
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C50/00—Quinones
    • C07C50/24—Quinones containing halogen

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The present invention provides a compound selected from the group consisting of (I), (II), and (III), wherein R?1 and R4¿ are the same or different and are each H, C¿1?-C3 alkyl, phosphate, or C1-C3 alkyl carboxylate; R?2 and R3¿ are the same or different and are each H, a halogen, A-Z, S-Z, S-A-Z, N(B)-Z, N(B)-A-Z, O-Z, or O-A-Z, wherein: A is a C¿1?-C20 linear or branched saturated or unsaturated alkyl, haloalkyl, arylalkyl, cycloalkylalkyl, heterocycloalkyl, hydroxyalkyl, alkoxyalkyl, thioalkyl, carboxyalkyl, carboalkoxyalkyl, carboxyaminoalkyl, a 5- to 6-membered ring carbohydrate or the corresponding acyclic analog thereof, peptidyl, or aminoalkyl diradical; B is H or C1-C6 alkyl; Z is H, aryl, heterocyclic, or a heteroatom-containing functional group; and R?5-R8¿ are the same or different and are each H, a halogen, heterocyclic, Z as defined above, A-Z as defined above, or heteroatom-containing functional group, provided that R5-R8 are not all H, useful as cellular growth inhibitors.
PCT/US1999/017863 1998-08-06 1999-08-06 Antiproliferative naphthoquinones, derivatives, compositions, and uses thereof WO2000008495A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU53416/99A AU5341699A (en) 1998-08-06 1999-08-06 Antiproliferative naphthoquinones, derivatives, compositions, and uses thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US12993298A 1998-08-06 1998-08-06
US09/129,932 1998-08-06

Publications (2)

Publication Number Publication Date
WO2000008495A2 WO2000008495A2 (en) 2000-02-17
WO2000008495A3 true WO2000008495A3 (en) 2000-05-25

Family

ID=22442272

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1999/017863 WO2000008495A2 (en) 1998-08-06 1999-08-06 Antiproliferative naphthoquinones, derivatives, compositions, and uses thereof

Country Status (2)

Country Link
AU (1) AU5341699A (en)
WO (1) WO2000008495A2 (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2093207A1 (en) * 2008-02-06 2009-08-26 Julius-Maximilians-Universität Würzburg Antiinfective and antitumoral compounds isolated from tropical lianas
AT509501B1 (en) 2010-02-24 2012-06-15 Univ Wien Tech PESTICIDES
WO2013016661A1 (en) * 2011-07-27 2013-01-31 Howard University Method for inhibiting trypansoma cruzi
EP2671574A1 (en) 2012-06-04 2013-12-11 VitaK B.V. Use of vitamin K to decrease allograft failure and patient mortality after organ transplantation
RU2499789C1 (en) * 2012-11-01 2013-11-27 Федеральное государственное бюджетное учреждение науки Институт химической биологии и фундаментальной медицины Сибирского отделения Российской академии наук (ИХБФМ СО РАН) Alkylating fluorinated 1,4-naphthoquinone derivatives having cytotoxic effect on human cancer cells in culture
NZ757526A (en) * 2017-04-21 2022-02-25 Univ Tasmania Naphthoquinones, their derivatives and uses thereof in methods for the treatment of mitochondrial dysfunction
CN107793380B (en) * 2017-10-30 2021-04-23 黑龙江八一农垦大学 2, 3-epoxy-2-propyl sulfone-5, 8-dimethoxy-1, 4-naphthoquinone, preparation method thereof and medicine containing same
CN107759538B (en) * 2017-10-30 2021-04-23 黑龙江八一农垦大学 2, 3-epoxy-2-nonane sulfone-5, 8-dimethoxy-1, 4-naphthoquinone, preparation method thereof and medicine containing same

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3344438A1 (en) * 1982-12-08 1984-06-14 L'oreal, Paris COLORING AGENT FOR KERATIN FIBERS, ESPECIALLY FOR HAIR
EP0150831A2 (en) * 1984-01-27 1985-08-07 Syntex (U.S.A.) Inc. Naphthalene anti-psoriatic agents
EP0226842A2 (en) * 1985-12-19 1987-07-01 American Cyanamid Company Substituted 1,4-naphthalenediones, processes for their preparation and pharmaceutical compositions containing them
EP0282056A2 (en) * 1987-03-11 1988-09-14 Syntex (U.S.A.) Inc. Naphthalene anti-psoriatic agents
EP0282006A1 (en) * 1987-03-09 1988-09-14 Syntex (U.S.A.) Inc. Naphtalene anti-psoriatic agents
DE3801743A1 (en) * 1987-07-03 1989-01-19 Bayer Ag PEST CONTROLS BASED ON SUBSTITUTED 1,4-NAPHTHOCHINONS AND NEW SUBSTITUTED 1,4-NAPHTHOCHINONES
WO1993017028A1 (en) * 1992-02-24 1993-09-02 Schinazi Raymond F Sensitizing agents for use in boron neutron capture therapy
FR2757386A1 (en) * 1996-12-23 1998-06-26 Oreal METHOD FOR TWO-STAGE OXIDATION DYEING OF KERATIN FIBERS WITH A SALT OR A MANGANESE COMPLEX AND A 4-SUBSTITUTED 1-NAPHTHOL AND STAINING KIT

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3344438A1 (en) * 1982-12-08 1984-06-14 L'oreal, Paris COLORING AGENT FOR KERATIN FIBERS, ESPECIALLY FOR HAIR
EP0150831A2 (en) * 1984-01-27 1985-08-07 Syntex (U.S.A.) Inc. Naphthalene anti-psoriatic agents
EP0226842A2 (en) * 1985-12-19 1987-07-01 American Cyanamid Company Substituted 1,4-naphthalenediones, processes for their preparation and pharmaceutical compositions containing them
EP0282006A1 (en) * 1987-03-09 1988-09-14 Syntex (U.S.A.) Inc. Naphtalene anti-psoriatic agents
EP0282056A2 (en) * 1987-03-11 1988-09-14 Syntex (U.S.A.) Inc. Naphthalene anti-psoriatic agents
DE3801743A1 (en) * 1987-07-03 1989-01-19 Bayer Ag PEST CONTROLS BASED ON SUBSTITUTED 1,4-NAPHTHOCHINONS AND NEW SUBSTITUTED 1,4-NAPHTHOCHINONES
WO1993017028A1 (en) * 1992-02-24 1993-09-02 Schinazi Raymond F Sensitizing agents for use in boron neutron capture therapy
FR2757386A1 (en) * 1996-12-23 1998-06-26 Oreal METHOD FOR TWO-STAGE OXIDATION DYEING OF KERATIN FIBERS WITH A SALT OR A MANGANESE COMPLEX AND A 4-SUBSTITUTED 1-NAPHTHOL AND STAINING KIT

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
J. MARKOVITS ET AL., INTERNATIONAL JOURNAL OF ONCOLOGY, vol. 13, no. 6, 1998, pages 1163 - 70, XP000864348 *
T. FREW ET AL., ANTI-CANCER DRUG DESIGN, vol. 10, no. 4, 1995, pages 347 - 59, XP000864349 *

Also Published As

Publication number Publication date
WO2000008495A2 (en) 2000-02-17
AU5341699A (en) 2000-02-28

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